4-(Hydroxymethyl)benzeneboronic acid → HCID 86653489、化合物

HRID 1888376ノート

反応式

HRID 1888376 の反応式
Br[C:2]1[CH:24]=[N:23][C:5]2[N:6]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[OH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>C(#N)C.[F-].[K+].O>[OH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:24]2[CH:2]=[CH:3][C:4]3[C:8]4[CH:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=4[N:6]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]=3[N:23]=2)=[CH:29][CH:28]=1

参加物

6

反応物 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 58266568HCID 58266568、化合物

生成物 1

HCID 86653489HCID 86653489、化合物収率 172.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 522689Potassium Fluoride溶媒

反応条件

温度
140 °C

実験手順

A mixture of 3-bromo-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (700 mg, 0.87 mmol), 4-hydroxymethylbenzeneboronic acid (400 mg, 1.32 mmol) and 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (52.5 mg, 0.064 mmol) in acetonitrile (21 mL) and 2N aqueous potassium fluoride solution (21 mL) was devided equally across two 25 mL microwave vials. Each vial was degassed with nitrogen for 10 minutes before the mixtures were heated under microwave irradiation at 140° C. for 30 minutes. The reaction mixtures were allowed to cool to ambient temperature, combined and diluted with water (50 mL). The precipitate was collected by filtration, washed with water (50 mL) and left to air dry. The resultant grey solid was purified by flash column chromatography (silica, 40 g column, ISCO, 0-100% ethyl acetate in cyclohexane). The isolated solid was then triturated with hot t-BME to afford the title compound as a light grey solid (646 mg, 26%). LCMS (Method B): RT=4.11 min, M+H+=431.

後処理

  1. customEach vial was degassed with nitrogen for 10 minutes before the mixtures
  2. customThe reaction mixtures
  3. temperatureto cool to ambient temperature
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (50 mL)
  6. waitleft to air
  7. customdry
  8. customThe resultant grey solid was purified by flash column chromatography (silica, 40 g column, ISCO, 0-100% ethyl acetate in cyclohexane)
  9. customThe isolated solid was then triturated with hot t-BME

出典と根拠

ORDレコード
ord-e158a64d2afd46b39267764c0a8701c9
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

読み込み中…